Vacation rentals in Shelbyville

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Top-rated vacation rentals in Shelbyville

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Guest favorite

Apartment in Simpsonville

4.98 out of 5 average rating, 130 reviews

Ridgecrest Estate. Comfort and convenience.

A newly renovated 650-sq-ft. upstairs apartment with private entrance. Property sits on 5 acres in the heart of the Saddlebred Capital of the world. Just 9 miles east of the Watterson Expressway, Ridgecrest estate is an ideal location for enjoying the best of Kentucky in a quiet and peaceful environment. Quick access to I-64 (1/4 mile); 45 min. to Keeneland, 30 min to Churchill Downs, and 2 min to the Outlet Shoppes. No children under 13. Additional guests more than 2, $20 extra per night.

Guest favorite

Chalet in Lawrenceburg

4.97 out of 5 average rating, 147 reviews

Countryside On the Bourbon Trail, 22 Quiet Acres

Welcome to Sea Glass Farm. 1900's restored farmhouse with tons of charm! Full access to 22 acres with beautiful hilltop sunsets. In the heart of The Bourbon Trail, the scenery and wildlife will not disappoint. The location is perfect for a rural getaway or relaxing stop on your Bourbon Trail experience. Minutes from shopping and restaurants; situated between I-64 and The Bluegrass Parkway. This place has been a dream of ours and it will soon be in your dreams as well. Hosted by the owner!

Superhost

Home in Shelbyville

4.8 out of 5 average rating, 115 reviews

Parris on Main

Parris on Main Street is the perfect location to enjoy the historic town of Shelbyville and, a few blocks walking distance to many antique shops, local coffee houses and great locations to grab a bite to eat. **Update - brand new ac system installed 7/19/2023 Newly renovated, built in 1942, this house is perfect for a family or group of friends wanting to experience the wonderful places Kentucky has to offer. Right in the middle the Bourbon Trail and about 30 minutes from ChurchIll Downs

Guest favorite

Guest suite in Shelbyville

4.97 out of 5 average rating, 33 reviews

Spacious suite, country views, pool table, firepit

Escape to the tranquility of the countryside at Marshalls Creekside Haven. Our lower-level walkout guest suite, with own driveway and entrance, offers the perfect retreat, providing comfort and relaxation. Enjoy the warm glow of the fire pit or sway gently on the porch swing, taking in the breathtaking country views that surround you. Indoors enjoy a game of pool, darts or board games. Convenient to bourbon trail, wineries and quaint towns. Cell service is AT&T. Wi-Fi provided by Starlink.

Guest favorite

Barn in Mount Eden

4.98 out of 5 average rating, 119 reviews

Sweet Hollow Farm

Sweet Hollow Farm is located near Taylorsville Lake. 30 miles from Louisville, 40 miles from Lexington and 25 from Bardstown. We have a small farm with a studio barn apartment. Private entrance with full bath. We also have a beautiful pool that we share with our guests. There is a horseshoe pit, fire pit and multiple outdoor seating areas. Kids and dogs are welcome. We even have space for horses and boats. We can offer peace and quiet, a clear view of the stars and hummingbird theatrics.

Guest favorite

Tiny home in La Grange

4.97 out of 5 average rating, 159 reviews

Brakeman's Cottage

"All Aboard the Brakeman's Cottage! Experience the charm of this tiny house listed on the National Register of Historic Buildings in LaGrange, Kentucky. Nestled just feet from the train tracks in the heart of downtown, it offers a unique experience. Situated across from the train observation tower and within walking distance of the best restaurants and quaint shops, our newly remodeled property features private off-street parking. Step into history with modern comforts at Brakeman's

Guest favorite

Condo in Shelbyville

4.89 out of 5 average rating, 109 reviews

Your Kentucky Home Away From Home

Lovely, renovated Patio Home features 2 bedrooms and 2 full baths – one with a low-entrance shower and one with a full tub. This Open Floor Plan has 1st Floor Entry, front-door parking and 36” doors, making it easily accessible. This home is fully furnished throughout, including a full kitchen with all appliances, dishes, drinkware and silverware, washer and dryer, wall-mounted flat-screen television, tasteful art, linens, towels and more. This is your home away from home!

Guest favorite

Loft in Shelbyville

4.98 out of 5 average rating, 103 reviews

Bottled in Bond: Perfect Bourbon Trail Location

FEATURED on HGTV! Swanky! Stunning! Spectacular! You'll be in a top-floor loft overlooking downtown Shelbyville and perfectly situated in the heart of the Bourbon Trail! Incredible place to stay for Derby, Keeneland, PGA or local weddings and events---if you can pry yourself away from here! We specialize in making your stay an over-the-top experience and are happy to arrange chauffeured transportation, private chef accommodations, and dinner reservations.

Guest favorite

Cabin in Lawrenceburg

4.98 out of 5 average rating, 442 reviews

Bourbon Trail Cabin on the Farm

Recognized by AirBnB as the “2021 Top New AirBnB in the State of KY”!Overlooking rolling hay fields, and surrounded by wooded farm land, this cabin features barn wood walls, hardwood floors, handcrafted bourbon barrel sink, king bed, leather sleeper sofa, and custom built kitchenette. Located on a working cattle farm, see cows, goats, a donkey and horse, & our pet free-range pig! In the heart of the Bourbon Trail in the home of Wild Turkey and Four Roses.

Guest favorite

Cottage in Pleasureville

4.99 out of 5 average rating, 174 reviews

The Cozy Cottage on One Goat Farm

This quaint little cottage is located on the Bourbon Trail of Kentucky. A mere 9 minutes from Six-Mile Distillery, it is also in close proximity to a gas station, grocery and library. Located in the heart of an Amish community, you will hear horses and buggies clip-clopping past as you sip your morning coffee. This cottage is on a functioning farm with horses, cats, goats and donkeys, with overnight housing facilities for your own equines as well.

Guest favorite

Cabin in Mount Eden

4.97 out of 5 average rating, 107 reviews

Bourbon Country Cottage

Newly renovated cottage located in the country. Enjoy amazing views from the porch while enjoying the outdoor patio. Fully furnished to make your stay comfortable and delightful. Memory foam mattresses for wonderful sleep and a well equipped kitchen for cooking. Enjoy exploring the walking trails, creek and the 80 acre property while you stay. Stocked Fishing Pond Check out our other listing too, Bourbon Country Cabin, same property.

Guest favorite

Farm stay in Goshen

4.98 out of 5 average rating, 286 reviews

The Coop

This 2 bedroom house is a renovated old farmhouse located on the site of a small vegetable farm and native plant nursery. The back deck overlooks the woods, where you can watch the wild birds and keep an eye on the free range chickens. This is a quiet spot for a retreat, but also 25 minutes from downtown Louisville. The Coop has a fully stocked kitchen and comes with eggs right from our flock....

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Shelbyville vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Shelbyville's top sights

Walmart Supercenter4 locals recommend

Claudia Sanders Dinner House16 locals recommend

Cracker Barrel Old Country Store5 locals recommend

Jeptha Creed Distillery36 locals recommend

La Cocina de Mama12 locals recommend

Milano Italian Restaurant3 locals recommend

Other great vacation rentals in Shelbyville

Guest favorite

Guest suite in Shelbyville

5.0 out of 5 average rating, 61 reviews

Comfortable Charm on the Bourbon Trail & 2024 PGA

Guest favorite

Farm stay in Shelbyville

5.0 out of 5 average rating, 16 reviews

Bourbon trail apartment on horse farm

Guest favorite

Guesthouse in Shelbyville

4.96 out of 5 average rating, 71 reviews

Cottage of Eden. Bourbon Trail Stay in Shelby Co.

Guest favorite

Home in Shelbyville

4.85 out of 5 average rating, 39 reviews

Bourbon Basecamp! New on the Bourbon Trail!

Guest favorite

Home in Shelbyville

5.0 out of 5 average rating, 17 reviews

oasis 522

Guest favorite

Cabin in Lawrenceburg

4.97 out of 5 average rating, 29 reviews

Hidden View Cabin

Guest favorite

Home in Shelbyville

5.0 out of 5 average rating, 11 reviews

Pool*HOT TUB*Bourbon Trail

Superhost

Home in Simpsonville

4.87 out of 5 average rating, 85 reviews

Charming 4 Bedroom classic home bourbon trail!

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Quick stats about vacation rentals in Shelbyville

Total rentals
40 properties
Wifi availability
40 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
1.6K reviews
Nightly prices starting at
$30 before taxes and fees

Frequently Asked Questions

Do house rentals in Shelbyville have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Shelbyville. Enjoy a tailored experience with all the comforts you desire.
Are there vacation rentals with a dedicated workspace in Shelbyville?
Yes! Work meets play with ease at over 20 vacation rentals in Shelbyville featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Shelbyville?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with air conditioning, over 20 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Shelbyville have wireless internet?
Absolutely! We offer over 20 house rentals with wireless internet in Shelbyville. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Shelbyville?
Experience the best of Shelbyville with our house rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly vacation rentals in Shelbyville?
Shelbyville has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

Vacation rentals in Shelbyville

Top-rated vacation rentals in Shelbyville

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Shelbyville vacation rentals

Stay near Shelbyville's top sights

Other great vacation rentals in Shelbyville

Guest suite in Shelbyville

Farm stay in Shelbyville

Guesthouse in Shelbyville

Home in Shelbyville

Home in Shelbyville

Cabin in Lawrenceburg

Home in Shelbyville

Home in Simpsonville

Quick stats about vacation rentals in Shelbyville

Total rentals

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Shelbyville have air conditioning?

Are there vacation rentals with a dedicated workspace in Shelbyville?

What are the most popular amenities for House Rentals in Shelbyville?

Do house rentals in Shelbyville have wireless internet?

How much does it cost to stay in house rentals in Shelbyville?

Are there family-friendly vacation rentals in Shelbyville?

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